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In the title compound, C16H15N5·4H2O, the two independent mol­ecules of the asymmetric unit are linked into a three-dimensional structure by a combination of classical hydrogen bonds, C—H...π and aromatic π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033721/tk2069sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033721/tk2069IIsup2.hkl
Contains datablock II

CCDC reference: 621512

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.068
  • wR factor = 0.160
  • Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C1 - C6 .. 9.29 su PLAT417_ALERT_2_B Short Inter D-H..H-D H1 .. H4B .. 1.44 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H1B .. H6B .. 1.29 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H2A .. H6A .. 1.67 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H3A .. H4A .. 2.09 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H5B .. H10 .. 1.63 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT128_ALERT_4_C Non-standard setting of Space group Pca21 .... Pbc21 PLAT230_ALERT_2_C Hirshfeld Test Diff for N8 - C26 .. 5.09 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C24 .. 6.90 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 3608 Count of symmetry unique reflns 3615 Completeness (_total/calc) 99.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 6 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Bis(benzimidazol-2-ylmethyl)amine tetrahydrate top
Crystal data top
C16H15N5·4H2OF(000) = 1488
Mr = 349.39Dx = 1.286 Mg m3
Orthorhombic, Pbc21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2bCell parameters from 6949 reflections
a = 4.7111 (6) Åθ = 2.6–23.4°
b = 24.857 (3) ŵ = 0.09 mm1
c = 30.823 (4) ÅT = 292 K
V = 3609.5 (8) Å3Block, yellow
Z = 80.40 × 0.20 × 0.06 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3608 independent reflections
Radiation source: fine focus sealed Siemens Mo tube3171 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 55
Tmin = 0.963, Tmax = 0.994k = 3028
25072 measured reflectionsl = 3838
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + (0.0776P)2 + 1.7967P]
where P = (Fo2 + 2Fc2)/3
3608 reflections(Δ/σ)max = 0.005
451 parametersΔρmax = 0.33 e Å3
1 restraintΔρmin = 0.23 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.0059 (9)0.7488 (2)0.8491 (2)0.0328 (15)
C21.1384 (13)0.7939 (2)0.8322 (2)0.0443 (14)
H21.09140.80780.80510.053*
C31.3433 (13)0.8168 (2)0.8578 (2)0.0482 (15)
H31.43410.84760.84780.058*
C41.4224 (14)0.7963 (2)0.8981 (2)0.0458 (14)
H41.56820.81240.91370.055*
C51.2820 (12)0.7513 (3)0.9150 (2)0.0461 (14)
H51.33010.73780.94210.055*
C61.0681 (12)0.7271 (2)0.89030 (16)0.0298 (11)
C70.7444 (10)0.67620 (19)0.86279 (15)0.0294 (10)
C80.5348 (10)0.6335 (2)0.8539 (2)0.0300 (12)
H8A0.37880.64810.83710.036*
H8B0.45880.62000.88110.036*
C90.8191 (11)0.5505 (2)0.85801 (18)0.0367 (12)
H9A0.94620.57020.87700.044*
H9B0.93400.52690.84010.044*
C100.6259 (11)0.5169 (2)0.88515 (17)0.0328 (11)
C110.3109 (10)0.45932 (19)0.90504 (16)0.0298 (10)
C120.1107 (12)0.4185 (2)0.90736 (19)0.0418 (13)
H120.05560.39890.88310.050*
C130.0029 (14)0.4087 (3)0.9484 (3)0.0490 (18)
H130.13250.38070.95160.059*
C140.0658 (15)0.4374 (3)0.9832 (2)0.0542 (18)
H140.02570.42981.00920.065*
C150.2640 (14)0.4777 (3)0.98275 (18)0.0503 (15)
H150.31360.49671.00760.060*
C160.3866 (11)0.4883 (2)0.94235 (17)0.0345 (12)
C170.0482 (13)0.8820 (3)0.6468 (2)0.0405 (14)
H17A0.10900.89510.66410.049*
H17B0.02800.86910.61950.049*
C180.2482 (10)0.9268 (2)0.63827 (16)0.0323 (11)
C190.5003 (11)0.9986 (3)0.65140 (17)0.0351 (15)
C200.6237 (13)1.0457 (2)0.6668 (2)0.0433 (13)
H200.56801.06070.69310.052*
C210.8295 (13)1.0690 (2)0.6420 (2)0.0501 (15)
H210.92031.09990.65180.060*
C220.9059 (13)1.0466 (3)0.6015 (2)0.0499 (16)
H221.04601.06320.58510.060*
C230.7794 (11)1.0012 (2)0.58610 (18)0.0400 (12)
H230.82940.98700.55930.048*
C240.5740 (11)0.9770 (2)0.61157 (18)0.0314 (12)
C250.3440 (11)0.8009 (2)0.64126 (19)0.0385 (12)
H25A0.46010.77740.65900.046*
H25B0.46960.82160.62270.046*
C260.1506 (10)0.7674 (2)0.61355 (17)0.0317 (11)
C270.1619 (10)0.70960 (18)0.59437 (15)0.0278 (10)
C280.3617 (11)0.6687 (2)0.59237 (19)0.0381 (12)
H280.40640.64880.61700.046*
C290.4906 (12)0.6581 (3)0.5543 (3)0.0437 (17)
H290.62780.63130.55290.052*
C300.4201 (14)0.6874 (3)0.5159 (2)0.0500 (16)
H300.50430.67830.48960.060*
C310.2264 (12)0.7294 (2)0.51769 (19)0.0433 (13)
H310.18360.74960.49320.052*
C320.0971 (11)0.7403 (2)0.55773 (16)0.0305 (11)
O10.4748 (9)0.44309 (19)0.78393 (14)0.0493 (12)
H1A0.62300.45850.77690.074*
H1B0.34250.46450.78460.074*
O20.0888 (11)0.59640 (18)0.76511 (17)0.0632 (13)
H2A0.04870.58750.75010.095*
H2B0.15110.62540.75630.095*
O30.0683 (11)0.6945 (2)0.71456 (17)0.0601 (13)
H3A0.05860.69660.73290.090*
H3B0.00140.69990.69020.090*
O40.5653 (10)0.7357 (2)0.75034 (19)0.0648 (14)
H4A0.67600.76130.74790.097*
H4B0.51950.73170.77560.097*
O50.6104 (10)0.84591 (19)0.73494 (16)0.0613 (12)
H5B0.47930.84770.71710.092*
H5C0.57740.86690.75510.092*
O60.0209 (9)0.48752 (18)0.74986 (15)0.0435 (10)
H6A0.01520.52050.74890.065*
H6B0.12560.47570.76080.065*
O70.8412 (8)0.61756 (16)0.97301 (12)0.0461 (10)
H7A0.96660.62150.99140.069*
H7B0.87450.63680.95190.069*
O80.3434 (8)0.86930 (16)0.52654 (12)0.0455 (9)
H8C0.32810.89360.54450.068*
H8D0.50470.86910.51620.068*
N10.7999 (9)0.71513 (16)0.83295 (13)0.0345 (10)
H10.72300.71540.80770.041*
N20.9042 (10)0.68157 (17)0.89778 (14)0.0328 (9)
N30.4654 (11)0.4802 (2)0.8693 (2)0.0440 (14)
N40.5816 (11)0.52549 (17)0.92827 (14)0.0335 (10)
H4C0.67390.55160.93990.040*
N50.6689 (9)0.58898 (18)0.82977 (14)0.0358 (10)
H5A0.52210.57560.81260.043*
N60.2924 (9)0.96564 (16)0.66822 (14)0.0331 (9)
H60.20140.97270.69170.040*
N70.4102 (10)0.93178 (19)0.60369 (13)0.0339 (10)
N80.0049 (8)0.72676 (16)0.62888 (15)0.0219 (9)
N90.1044 (9)0.77626 (19)0.57090 (14)0.0344 (10)
H90.21240.79530.55440.041*
N100.1853 (9)0.83765 (18)0.66937 (14)0.0362 (10)
H100.17950.82870.69550.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.023 (3)0.011 (2)0.064 (4)0.0040 (17)0.007 (2)0.006 (3)
C20.052 (4)0.029 (3)0.052 (3)0.001 (3)0.005 (3)0.002 (3)
C30.044 (3)0.032 (3)0.069 (4)0.010 (2)0.013 (3)0.010 (3)
C40.049 (3)0.035 (3)0.053 (4)0.006 (3)0.001 (3)0.014 (3)
C50.038 (3)0.053 (3)0.048 (3)0.006 (3)0.005 (3)0.019 (3)
C60.036 (3)0.029 (3)0.025 (3)0.003 (2)0.007 (2)0.002 (2)
C70.032 (3)0.029 (3)0.027 (2)0.005 (2)0.000 (2)0.0004 (19)
C80.024 (2)0.029 (3)0.037 (3)0.001 (2)0.001 (2)0.004 (3)
C90.031 (3)0.038 (3)0.041 (3)0.000 (2)0.008 (2)0.002 (2)
C100.030 (3)0.032 (3)0.037 (3)0.004 (2)0.000 (2)0.000 (2)
C110.032 (3)0.026 (2)0.032 (2)0.004 (2)0.001 (2)0.002 (2)
C120.048 (3)0.029 (3)0.048 (3)0.009 (2)0.004 (3)0.008 (3)
C130.053 (4)0.043 (4)0.052 (4)0.009 (3)0.015 (3)0.006 (4)
C140.066 (4)0.050 (4)0.046 (4)0.018 (3)0.027 (3)0.009 (3)
C150.062 (4)0.061 (4)0.028 (3)0.002 (3)0.003 (3)0.002 (3)
C160.031 (3)0.034 (3)0.039 (3)0.001 (2)0.006 (2)0.002 (2)
C170.033 (3)0.041 (4)0.047 (4)0.002 (2)0.004 (3)0.001 (3)
C180.029 (3)0.034 (3)0.035 (3)0.006 (2)0.008 (2)0.003 (2)
C190.045 (3)0.050 (4)0.010 (2)0.005 (2)0.0058 (18)0.000 (2)
C200.050 (3)0.039 (3)0.041 (3)0.004 (3)0.010 (3)0.003 (3)
C210.052 (4)0.038 (3)0.060 (4)0.004 (3)0.019 (3)0.001 (3)
C220.034 (3)0.055 (4)0.061 (4)0.005 (3)0.011 (3)0.025 (3)
C230.041 (3)0.045 (3)0.034 (3)0.002 (3)0.002 (2)0.006 (2)
C240.024 (2)0.036 (3)0.035 (3)0.002 (2)0.013 (2)0.011 (2)
C250.032 (3)0.035 (3)0.049 (3)0.002 (2)0.008 (2)0.002 (2)
C260.027 (3)0.029 (3)0.039 (3)0.005 (2)0.002 (2)0.003 (2)
C270.027 (2)0.025 (2)0.031 (2)0.0003 (19)0.000 (2)0.002 (2)
C280.037 (3)0.030 (3)0.048 (3)0.006 (2)0.004 (2)0.001 (2)
C290.039 (4)0.033 (4)0.059 (5)0.006 (2)0.007 (3)0.005 (4)
C300.046 (3)0.058 (4)0.046 (4)0.003 (3)0.008 (3)0.008 (3)
C310.047 (3)0.047 (3)0.036 (3)0.012 (3)0.002 (3)0.001 (3)
C320.036 (3)0.022 (2)0.034 (3)0.000 (2)0.005 (2)0.001 (2)
O10.055 (3)0.061 (3)0.032 (2)0.005 (2)0.0010 (18)0.012 (2)
O20.078 (3)0.046 (3)0.066 (3)0.001 (2)0.021 (3)0.004 (2)
O30.057 (3)0.070 (3)0.053 (3)0.006 (2)0.000 (2)0.017 (3)
O40.060 (3)0.081 (4)0.054 (3)0.005 (3)0.016 (2)0.001 (3)
O50.067 (3)0.061 (3)0.057 (3)0.001 (3)0.014 (2)0.006 (2)
O60.064 (3)0.033 (2)0.034 (2)0.0043 (17)0.0004 (18)0.0065 (18)
O70.047 (2)0.054 (2)0.037 (2)0.0138 (19)0.0022 (17)0.0034 (18)
O80.051 (2)0.047 (2)0.038 (2)0.0120 (18)0.0026 (18)0.0016 (18)
N10.043 (3)0.033 (2)0.027 (2)0.0043 (19)0.0049 (19)0.0013 (18)
N20.037 (2)0.030 (2)0.032 (2)0.001 (2)0.000 (2)0.0005 (18)
N30.039 (3)0.046 (3)0.047 (3)0.004 (2)0.002 (2)0.008 (3)
N40.044 (3)0.026 (2)0.030 (2)0.009 (2)0.0025 (19)0.0042 (18)
N50.038 (2)0.040 (2)0.029 (2)0.005 (2)0.0014 (19)0.0004 (19)
N60.035 (2)0.035 (2)0.029 (2)0.0026 (19)0.0027 (18)0.0019 (18)
N70.033 (2)0.041 (3)0.027 (2)0.006 (2)0.0018 (19)0.0052 (19)
N80.031 (2)0.014 (2)0.021 (2)0.0017 (14)0.0015 (14)0.0053 (18)
N90.028 (2)0.040 (3)0.035 (2)0.009 (2)0.0002 (19)0.005 (2)
N100.039 (2)0.040 (3)0.030 (2)0.004 (2)0.0041 (19)0.0031 (19)
Geometric parameters (Å, º) top
C1—N11.375 (7)C21—C221.411 (10)
C1—C21.384 (8)C21—H210.9300
C1—C61.410 (9)C22—C231.362 (9)
C2—C31.371 (9)C22—H220.9300
C2—H20.9300C23—C241.384 (8)
C3—C41.392 (10)C23—H230.9300
C3—H30.9300C24—N71.384 (7)
C4—C51.399 (9)C25—N101.464 (7)
C4—H40.9300C25—C261.501 (7)
C5—C61.398 (8)C25—H25A0.9700
C5—H50.9300C25—H25B0.9700
C6—N21.390 (7)C26—N81.334 (6)
C7—N21.322 (6)C26—N91.351 (7)
C7—N11.361 (6)C27—N81.364 (7)
C7—C81.476 (7)C27—C281.387 (7)
C8—N51.476 (7)C27—C321.397 (7)
C8—H8A0.9700C28—C291.348 (9)
C8—H8B0.9700C28—H280.9300
C9—N51.475 (7)C29—C301.428 (10)
C9—C101.492 (7)C29—H290.9300
C9—H9A0.9700C30—C311.387 (9)
C9—H9B0.9700C30—H300.9300
C10—N31.280 (7)C31—C321.403 (8)
C10—N41.362 (7)C31—H310.9300
C11—C121.387 (7)C32—N91.366 (7)
C11—C161.404 (7)O1—H1A0.8253
C11—N31.418 (8)O1—H1B0.8206
C12—C131.395 (9)O2—H2A0.8256
C12—H120.9300O2—H2B0.8257
C13—C141.329 (11)O3—H3A0.8246
C13—H130.9300O3—H3B0.8259
C14—C151.370 (9)O4—H4A0.8260
C14—H140.9300O4—H4B0.8150
C15—C161.398 (8)O5—H5B0.8284
C15—H150.9300O5—H5C0.8254
C16—N41.373 (7)O6—H6A0.8219
C17—N101.454 (8)O6—H6B0.8228
C17—C181.483 (8)O7—H7A0.8251
C17—H17A0.9700O7—H7B0.8227
C17—H17B0.9700O8—H8C0.8222
C18—N71.317 (7)O8—H8D0.8244
C18—N61.351 (7)N1—H10.8594
C19—N61.378 (8)N4—H4C0.8589
C19—C241.384 (8)N5—H5A0.9311
C19—C201.391 (9)N6—H60.8597
C20—C211.365 (9)N9—H90.8602
C20—H200.9300N10—H100.8363
N1—C1—C2132.4 (6)C20—C21—C22120.6 (6)
N1—C1—C6103.9 (5)C20—C21—H21119.7
C2—C1—C6123.7 (5)C22—C21—H21119.7
C3—C2—C1115.9 (6)C23—C22—C21121.6 (6)
C3—C2—H2122.1C23—C22—H22119.2
C1—C2—H2122.1C21—C22—H22119.2
C2—C3—C4123.4 (6)C22—C23—C24117.9 (6)
C2—C3—H3118.3C22—C23—H23121.0
C4—C3—H3118.3C24—C23—H23121.0
C3—C4—C5119.9 (6)N7—C24—C23130.1 (5)
C3—C4—H4120.1N7—C24—C19109.3 (5)
C5—C4—H4120.1C23—C24—C19120.6 (5)
C6—C5—C4118.8 (6)N10—C25—C26111.9 (4)
C6—C5—H5120.6N10—C25—H25A109.2
C4—C5—H5120.6C26—C25—H25A109.2
N2—C6—C5131.4 (5)N10—C25—H25B109.2
N2—C6—C1110.2 (4)C26—C25—H25B109.2
C5—C6—C1118.4 (5)H25A—C25—H25B107.9
N2—C7—N1111.7 (4)N8—C26—N9112.3 (5)
N2—C7—C8127.2 (5)N8—C26—C25123.5 (5)
N1—C7—C8121.0 (5)N9—C26—C25124.1 (5)
C7—C8—N5110.3 (4)N8—C27—C28129.2 (5)
C7—C8—H8A109.6N8—C27—C32109.9 (4)
N5—C8—H8A109.6C28—C27—C32120.8 (5)
C7—C8—H8B109.6C29—C28—C27119.2 (5)
N5—C8—H8B109.6C29—C28—H28120.4
H8A—C8—H8B108.1C27—C28—H28120.4
N5—C9—C10113.7 (4)C28—C29—C30121.2 (5)
N5—C9—H9A108.8C28—C29—H29119.4
C10—C9—H9A108.8C30—C29—H29119.4
N5—C9—H9B108.8C31—C30—C29120.2 (6)
C10—C9—H9B108.8C31—C30—H30119.9
H9A—C9—H9B107.7C29—C30—H30119.9
N3—C10—N4113.1 (5)C30—C31—C32117.8 (5)
N3—C10—C9123.0 (5)C30—C31—H31121.1
N4—C10—C9123.5 (5)C32—C31—H31121.1
C12—C11—C16120.4 (5)N9—C32—C27105.6 (4)
C12—C11—N3131.1 (5)N9—C32—C31133.6 (5)
C16—C11—N3108.5 (5)C27—C32—C31120.7 (5)
C11—C12—C13115.9 (5)H1A—O1—H1B110.4
C11—C12—H12122.1H2A—O2—H2B109.1
C13—C12—H12122.1H3A—O3—H3B109.7
C14—C13—C12122.9 (6)H4A—O4—H4B110.4
C14—C13—H13118.5H5B—O5—H5C109.0
C12—C13—H13118.5H6A—O6—H6B110.1
C13—C14—C15123.5 (6)H7A—O7—H7B109.8
C13—C14—H14118.2H8C—O8—H8D110.2
C15—C14—H14118.2C7—N1—C1108.9 (5)
C14—C15—C16115.3 (6)C7—N1—H1122.5
C14—C15—H15122.3C1—N1—H1128.5
C16—C15—H15122.3C7—N2—C6105.3 (4)
N4—C16—C15133.2 (5)C10—N3—C11105.6 (5)
N4—C16—C11104.9 (4)C10—N4—C16107.8 (4)
C15—C16—C11121.9 (5)C10—N4—H4C116.7
N10—C17—C18111.9 (5)C16—N4—H4C135.6
N10—C17—H17A109.2C9—N5—C8113.2 (4)
C18—C17—H17A109.2C9—N5—H5A117.4
N10—C17—H17B109.2C8—N5—H5A103.6
C18—C17—H17B109.2C18—N6—C19106.1 (5)
H17A—C17—H17B107.9C18—N6—H6130.1
N7—C18—N6113.4 (5)C19—N6—H6123.4
N7—C18—C17125.6 (5)C18—N7—C24104.9 (4)
N6—C18—C17120.9 (5)C26—N8—C27105.0 (4)
N6—C19—C24106.3 (5)C26—N9—C32107.1 (4)
N6—C19—C20132.0 (5)C26—N9—H9124.7
C24—C19—C20121.7 (6)C32—N9—H9126.6
C21—C20—C19117.6 (6)C17—N10—C25114.6 (5)
C21—C20—H20121.2C17—N10—H10130.3
C19—C20—H20121.2C25—N10—H10114.9
N1—C1—C2—C3178.4 (5)C28—C29—C30—C313.2 (10)
C6—C1—C2—C31.1 (8)C29—C30—C31—C322.3 (9)
C1—C2—C3—C41.4 (9)N8—C27—C32—N90.4 (6)
C2—C3—C4—C52.7 (9)C28—C27—C32—N9180.0 (5)
C3—C4—C5—C61.5 (9)N8—C27—C32—C31178.3 (5)
C4—C5—C6—N2176.9 (5)C28—C27—C32—C312.0 (8)
C4—C5—C6—C10.8 (8)C30—C31—C32—N9177.5 (6)
N1—C1—C6—N20.6 (6)C30—C31—C32—C270.2 (8)
C2—C1—C6—N2179.0 (5)N2—C7—N1—C10.8 (6)
N1—C1—C6—C5177.4 (5)C8—C7—N1—C1178.8 (4)
C2—C1—C6—C52.2 (8)C2—C1—N1—C7179.6 (6)
N2—C7—C8—N592.7 (6)C6—C1—N1—C70.1 (5)
N1—C7—C8—N585.1 (6)N1—C7—N2—C61.1 (6)
N5—C9—C10—N369.8 (7)C8—C7—N2—C6179.0 (5)
N5—C9—C10—N4103.5 (6)C5—C6—N2—C7177.4 (6)
C16—C11—C12—C130.6 (8)C1—C6—N2—C71.0 (6)
N3—C11—C12—C13179.3 (6)N4—C10—N3—C114.2 (6)
C11—C12—C13—C142.4 (10)C9—C10—N3—C11178.1 (5)
C12—C13—C14—C153.3 (12)C12—C11—N3—C10178.8 (5)
C13—C14—C15—C162.0 (11)C16—C11—N3—C102.5 (6)
C14—C15—C16—N4177.8 (6)N3—C10—N4—C164.4 (7)
C14—C15—C16—C110.2 (9)C9—C10—N4—C16178.2 (5)
C12—C11—C16—N4178.9 (5)C15—C16—N4—C10179.3 (6)
N3—C11—C16—N40.1 (6)C11—C16—N4—C102.5 (6)
C12—C11—C16—C150.4 (8)C10—C9—N5—C870.3 (6)
N3—C11—C16—C15178.5 (5)C7—C8—N5—C983.4 (5)
N10—C17—C18—N788.8 (7)N7—C18—N6—C190.2 (6)
N10—C17—C18—N686.7 (6)C17—C18—N6—C19176.3 (5)
N6—C19—C20—C21179.7 (6)C24—C19—N6—C180.7 (6)
C24—C19—C20—C212.5 (8)C20—C19—N6—C18177.3 (6)
C19—C20—C21—C221.9 (9)N6—C18—N7—C240.3 (6)
C20—C21—C22—C230.4 (9)C17—C18—N7—C24175.5 (5)
C21—C22—C23—C240.8 (8)C23—C24—N7—C18179.4 (5)
C22—C23—C24—N7178.7 (5)C19—C24—N7—C180.8 (6)
C22—C23—C24—C190.2 (8)N9—C26—N8—C271.2 (6)
N6—C19—C24—N71.0 (6)C25—C26—N8—C27176.1 (5)
C20—C19—C24—N7177.3 (5)C28—C27—N8—C26179.2 (5)
N6—C19—C24—C23179.7 (5)C32—C27—N8—C260.5 (5)
C20—C19—C24—C231.4 (8)N8—C26—N9—C321.4 (6)
N10—C25—C26—N873.2 (6)C25—C26—N9—C32175.8 (5)
N10—C25—C26—N9103.8 (6)C27—C32—N9—C261.0 (6)
N8—C27—C28—C29179.2 (5)C31—C32—N9—C26178.6 (6)
C32—C27—C28—C291.2 (8)C18—C17—N10—C2582.2 (6)
C27—C28—C29—C301.4 (9)C26—C25—N10—C1770.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O60.822.102.789 (7)142
O2—H2A···O60.832.492.795 (7)103
O2—H2B···O30.832.182.895 (7)145
O3—H3B···N80.832.002.782 (7)157
O4—H4A···O50.832.162.788 (8)133
O4—H4B···N10.822.242.823 (7)128
O5—H5B···N100.832.042.853 (6)169
O6—H6A···O20.822.012.795 (7)159
O6—H6B···O10.821.972.789 (7)176
O7—H7B···N20.822.012.828 (6)173
O8—H8C···N70.822.092.858 (6)155
N1—H1···O40.861.982.823 (7)166
N4—H4C···O70.862.092.939 (6)171
N5—H5A···O20.932.573.387 (7)148
N6—H6···O6i0.862.022.875 (6)175
N9—H9···O80.862.122.913 (6)153
N10—H10···O50.842.402.853 (6)114
O1—H1A···O6ii0.832.012.823 (6)169
O3—H3A···O4iii0.822.092.807 (7)145
O5—H5C···O1iv0.832.112.877 (7)155
O7—H7A···O8v0.832.092.903 (6)168
O8—H8D···O7vi0.822.102.886 (6)160
C8—H8B···Cg1iii0.972.853.545 (1)129
C17—H17A···Cg2iii0.972.953.612 (1)127
Symmetry codes: (i) x, y+1/2, z; (ii) x+1, y, z; (iii) x1, y, z; (iv) x+1, y+1/2, z; (v) x+1, y+3/2, z+1/2; (vi) x, y+3/2, z1/2.
 

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